Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK
About this cabin rental
Situated in Key West, this charming cabin for $1,381 per night is a great option for your next break. Tradewinds Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love? Located half a block from all the excitement of Duval Street, you can walk to historical landmarks like the Key West Lighthouse and The Ernest Hemingway Home and Museum, then stroll south to look out to sea from Southernmost Point. A short walk north will reveal more bars and restaurants than you could hope for on an island this size! Fuel your day with a home-cooked breakfast in your fully equipped kitchen, sip coffee in the tropical garden, and get a morning soak in the hot tub for some extra relaxation. Freshen up using the outdoor shower, have a barbecue using the gas grill, and kill some time browsing the free WiFi or surfing the flatscreen cable TV. A dog is welcome. Put life on hold for a moment and settle into paradise with these two cottages on Key West - book today! If you are bringing a dog on your trip, the nightly pet fee is already included in your quote when selecting "Yes" to pets. If you would like to add more dogs, please contact us. The nightly fee ranges between $150 and $200, depending on the bedroom count, and will apply for each additional dog. Parking notes: There is free parking available for 2 vehicles. Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit. More information can be downloaded from the "Rental Agreement" on the checkout page. Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation. County permit number: 25230-73041 (532 Olivia St) County permit number: 25230-102546 (529 Olivia St.)
Amenities
Air conditioner
Pets allowed
Kitchen / Kitchenette
Internet / Wifi
Hot Tub / Spa
Map of Key West, FL
Reviews
4.5/5.0
Excellent(86 Reviews)
2.0
Several AC issues caused considerable discomfort during entire stay. One bedroom AC leaked significantly into the bedroom and almost ruined a phone - I called the office and they sent a maintenance tech that temporarily fixed the leaking, but a night later water returned which we had to mop up with towels. Several floor AC units had been placed in hallway, but they did little to cool the hall and living areas, and they were extremely loud which made sleeping difficult. In addition, patio furniture was rusted so had to use towels to avoid staining clothes. Thankfully we only stayed 3 nights.
1.0
For the price; some updates should be done to the property; here are the issues we had:
-unit was dirty, floors were sticky, linens were dirty.
-some appliances were outdated
-Hole in the window above the bed, mosquito’s kept coming in before the storm hit, I had many bites all over me
-Ants in the kitchen
-Bed frame broken in one room
-beds were uncomfortable they had two divots in each of them where you could tell people had been sleeping in.
-The front door of the house had to be timed perfectly to open the door
-Door knob falling off in the back door
-the ac not working well at all in the bedroom closest to the front door
-the windows (able to put your hand through and look into the windows and touch)
-no cleaning supplies such as a broom for sweeping the floor due to sand getting everywhere, no extra paper towels, no cleaning spray once we got something in the counter we couldn’t sanitize which brought more ants
-fan does not work in the living room
-bathroom gets too hot due to the windows again
- the ironing board does not stand up or work
-the hot tub was not clean
-the cleaning lady just showed up during our vacation; if it's our house and we rented it really no one should be coming on the the property because how do we know if people are gonna come in or not and get our stuff and if they do come onto the property then we should get a warning about it.
-bathroom main light didn’t work
-front light did not work
Etc.
5.0
Clean, AC works, good water pressure. We came down for our Twins 21st birthday and had friends come along too. This place was how it is described.
4.0
The rental properties were very clean and close to everything. Shout out to the cleaning staff who were very kind and did a great job.
The air conditioner in our unit worked fine. The other unit next door had a portable unit connected to the window in addition to window units to make up for the sluggish bedroom air conditioning units. Unsightly but not a deal breaker.
Vacasa was not very helpful in allowing us in to our units even though the cleaning was complete. The code system is not the best and people in our group had trouble off and on our entire stay. When contacting the local vacasa person, they were dismissive and blamed the user when the unit's code box kept locking them out through no fault of their own.
We did like our unit and location but would not use Vacasa in the future.
5.0
The location of the two cottages was fantastic. We loved having both cottagesside by side-by-side with king size beds in all four bedrooms for our large group. The off the road parking was great. Loved the hottubs for late nights and early mornings.
5.0
Honestly this space worked well for our large extended family vacation. We took my mother for her 75th birthday celebration and everything was as pictured and described. Only one small issue and it was addressed quickly and to our comfort and satisfaction. Really appreciate the timely response time!
5.0
Cleanliness, communication, and location was some of the best aspects of the houses.
5.0
We rented these two cottages to celebrate my daughter’s 21st birthday. These cottages are wonderful. Well appointed, AC worked well, and it had everything we needed. We didn’t try the hot tubs, so I can’t speak to that. The employees at the local Vacasa office were wonderful to deal with.
5.0
Centrally located for a 15 minute walk to Duval Street, the beach, or the ferry.
4.0
The location couldn’t be better… within walking distance of essentially everything you’d want to do in Key West! One block off Duval St, and very close to some amazing eateries.
The checkin process was less than ideal… I kept scouring the VRBO app, the separate Vacasa app that was required to download and create a profile for in order to get the check-in instructions… only to find out that the door/access codes were not contained in either. Nor were these provided in any of the many emails ahead of time. Luckily, the property management company called about two hours before checkin to welcome us to the area (which was nice), but seemed very surprised that we had not been provided with the door codes. They gave them to us over the phone then.
The cottages were generally clean/tidy, but it became clear very quickly that the floors were VERY dirty. After walking across the floors barefoot a couple times, the bottom of one’s feet were borderline black from soot.
One of the units had a rotting floorboard inside near the front door… this was somewhat alarming, as it was flimsy enough that a misstep and one’s full body weight on the wrong spot would surely result in puncturing the floor to the crawl space beneath.
Otherwise, the units were great, the driveway was handy, and the outdoor seating areas were very pleasant. We’d probably consider staying here again if another trip to Key West were in our future.
4.0
Great location, but a couple comments
The location couldn’t be better… within walking distance of essentially everything you’d want to do in Key West! One block off Duval St, and very close to some amazing eateries.
The checkin process was less than ideal… I kept scouring the VRBO app, the separate Vacasa app that was required to download and create a profile for in order to get the check-in instructions… only to find out that the door/access codes were not contained in either. Nor were these provided in any of the many emails ahead of time. Luckily, the property management company called about two hours before checkin to welcome us to the area (which was nice), but seemed very surprised that we had not been provided with the door codes. They gave them to us over the phone then.
The cottages were generally clean/tidy, but it became clear very quickly that the floors were VERY dirty. After walking across the floors barefoot a couple times, the bottom of one’s feet were borderline black from soot.
One of the units had a rotting floorboard inside near the front door… this was somewhat alarming, as it was flimsy enough that a misstep and one’s full body weight on the wrong spot would surely result in puncturing the floor to the crawl space beneath.
Otherwise, the units were great, the driveway was handy, and the outdoor seating areas were very pleasant. We’d probably consider staying here again if another trip to Key West were in our future.
10.0
Clean, beautiful homes with new pumping AC units. Grilled our catch and ate it from the hot tub. Comfortable beds. Exceed expectations. Great location.
5.0
Great place
Clean, beautiful homes with new pumping AC units. Grilled our catch and ate it from the hot tub. Comfortable beds. Exceed expectations. Great location.
5.0
Clean, beautiful homes with new pumping AC units. Grilled our catch and ate it from the hot tub. Comfortable beds. Exceed expectations. Great location.
5.0
Great location!!
5.0
We had the best time visiting Key West! Staying here made our trip all the more memorable and special. Great location and an awesome set up for a larger group as the two cottages allow space for people to spread out.
5.0
Family Vacation
We had the best time visiting Key West! Staying here made our trip all the more memorable and special. Great location and an awesome set up for a larger group as the two cottages allow space for people to spread out.
5.0
Amazing Location!
Great location!!
5.0
The two cottages are perfectly situated for groups, with two king beds and a pullout couch in each, as well as a hot tub and grill! The location is very walkable to everything and an easy uber from the airport and golf course
5.0
Outstanding Space for a Group
The two cottages are perfectly situated for groups, with two king beds and a pullout couch in each, as well as a hot tub and grill! The location is very walkable to everything and an easy uber from the airport and golf course
5.0
This was our second after Christmas trip with the entire family. The houses are located very close to Duval and are convenient to shopping and restaurants.
5.0
Great houses
This was our second after Christmas trip with the entire family. The houses are located very close to Duval and are convenient to shopping and restaurants.
5.0
We rented both home for our group for the boat races. The check in process was smooth and easy and the homes were perfect! Quaint, cozy yet spacious and clean all with the historic Key West charm. We will be renting these homes from now on. Perfectly located a few steps from Duval. The hot tub was perfect after a long day out! Thank you for having such a great property! Everyone in our party of 8 was pleased!
5.0
Perfect properties
We rented both home for our group for the boat races. The check in process was smooth and easy and the homes were perfect! Quaint, cozy yet spacious and clean all with the historic Key West charm. We will be renting these homes from now on. Perfectly located a few steps from Duval. The hot tub was perfect after a long day out! Thank you for having such a great property! Everyone in our party of 8 was pleased!
4.0
Enjoyed the time
4.0
Enjoyed the houses. Driveway was to tight for larger car. Cleaning crew came to early and were a l
Enjoyed the time
5.0
We had 11 girls total in the house! We had the best time! The pull out bed needs to be replaced in the cabin on the left and the ac in the living rooms probably do too. The bedrooms were cold though! We enjoyed our trip!
5.0
Bachelorette trip
We had 11 girls total in the house! We had the best time! The pull out bed needs to be replaced in the cabin on the left and the ac in the living rooms probably do too. The bedrooms were cold though! We enjoyed our trip!
2.0
Both houses have Air conditioning issues. The living room AC is not enough to cool the area. We could not get it cooled below 80 and the bathroom felt like a sauna. The bedroom ACs cooled as long as the doors were shut but were so loud it would wake you every time it turned on. This was the case in both houses. Probably best not to stay in this property in the summer.
Also, even though we had no intention of using the hot tub in the summer we opened the covers just to check them out. One had missing pieces in the seat area and controllers that were so worn you couldn’t tell which button did what and the other was filthy with a funky smell and cloudy water.
We liked the location-it was right near Duval but still quiet. The outside gardens in the back were nice and tropical. The houses were also cute-just a shame we we’re miserably hot the entire time.
Of note-the street is very narrow with street parking right in front of the driveway that makes I difficult to pull in if you have a truck or large SUV.
5.0
These two houses fit our large group perfectly. And also perfectly located adjacent to Duval. Will be coming back here. Highly recommend
5.0
Absolutely wonderful stay
These two houses fit our large group perfectly. And also perfectly located adjacent to Duval. Will be coming back here. Highly recommend
2.0
Like the location but AC was terrible in both houses.
Both houses have Air conditioning issues. The living room AC is not enough to cool the area. We could not get it cooled below 80 and the bathroom felt like a sauna. The bedroom ACs cooled as long as the doors were shut but were so loud it would wake you every time it turned on. This was the case in both houses. Probably best not to stay in this property in the summer.
Also, even though we had no intention of using the hot tub in the summer we opened the covers just to check them out. One had missing pieces in the seat area and controllers that were so worn you couldn’t tell which button did what and the other was filthy with a funky smell and cloudy water.
We liked the location-it was right near Duval but still quiet. The outside gardens in the back were nice and tropical. The houses were also cute-just a shame we we’re miserably hot the entire time.
Of note-the street is very narrow with street parking right in front of the driveway that makes I difficult to pull in if you have a truck or large SUV.
4.0
The location is perfect. In the middle of everything. Just off Duval, up the street from the Hemingway museum, everything less than a mile away. Great layout of two cottages. Four total bedrooms, 2 bathrooms. Nice separation if needed. Only drawback was heat index was 102 and Air Conditioning struggled to keep up. Plus the Hot Tubs need some help, missing a few pieces. Also, two wifi setup, one worked, on didn't. The service was great, anything needed was just a call away, very responsive!
4.0
Tradewinds Key West Cottages
The location is perfect. In the middle of everything. Just off Duval, up the street from the Hemingway museum, everything less than a mile away. Great layout of two cottages. Four total bedrooms, 2 bathrooms. Nice separation if needed. Only drawback was heat index was 102 and Air Conditioning struggled to keep up. Plus the Hot Tubs need some help, missing a few pieces. Also, two wifi setup, one worked, on didn't. The service was great, anything needed was just a call away, very responsive!
3.0
Location was great. Good and bad was bar on nearby corner - great happy hours but not so great for late night noise. House needs a little attention to maintenence do to termites swarming.
3.0
Tradewinds Weekend
Location was great. Good and bad was bar on nearby corner - great happy hours but not so great for late night noise. House needs a little attention to maintenence do to termites swarming.
4.0
We rented the Leeward and Windward cottages for 7 nights. Along with our stay were some positives and negatives. (Beauty is in the eye of the beholder, so these things might not impact some visitors.)Parking found with this rental is rare as most rentals only provide 1 parking space far away or none at all. This property is GREAT for adults or families visiting that want to travel together, but want/need to SPREAD OUT with separate spaces. This rental is near a lot of great fine dining, and a quick walk to the most amazing Coffee/Cuban spot Key West Cuban Coffee (went there five days in a row). Location is good for those who want to be closer to the LGBTQ part of Key West. We rented bikes and it worked out just fine getting to the Northend of Duval. Not so good for light sleepers as the Leeward cottage bedrooms hear the party animals coming/going all night long, along with a bright security light shining into bedrooms that comes on each time a passerby comes along (every 5 minutes). Light sleepers need to stay in the Windward cottage as the bedrooms are not on the driveway side with bright light and noise traveling up the alley. If renting only one of these properties, the Windward is far superior with an open layout for congregating near the kitchen and a cleaned-up back patio. Neither of them are great for very many people gathering for drinks, dinner, or lunch as they do not have a dining room table. Important if you plan to cook and eat with each other. If you are like us and spent most of your time out-and-about then these work great. Items that may not influence most: Really liked the large mirrors in every room for making it easier for multiple people (girls) to get ready for an evening. We didn't use the hot tubs as it was super hot already in April. I'm not sure if that added expense of cottage with a hot tub fee is worth it unless in the winter. I want to note this is the first rental I've stayed in that didn't have a washer and dryer for us to use throughout the stay. Also, limited hangers and space for clothes and no dresser to put away clothes. For longer stays I felt these things are handy for not "living out of a suitcase."
5.0
Had an incredible experience at this rental property and would definitely visit again. Came down for a bachelor party (8 total guys) and had an absolute blast. Property team was incredibly helpful and easy to work with. GREAT location to everything.
4.0
Young adult women with a week-long stay
We rented the Leeward and Windward cottages for 7 nights. Along with our stay were some positives and negatives. (Beauty is in the eye of the beholder, so these things might not impact some visitors.)
Parking found with this rental is rare as most rentals only provide 1 parking space far away or none at all. This property is GREAT for adults or families visiting that want to travel together, but want/need to SPREAD OUT with separate spaces.
This rental is near a lot of great fine dining, and a quick walk to the most amazing Coffee/Cuban spot Key West Cuban Coffee (went there five days in a row). Location is good for those who want to be closer to the LGBTQ part of Key West. We rented bikes and it worked out just fine getting to the Northend of Duval.
Not so good for light sleepers as the Leeward cottage bedrooms hear the party animals coming/going all night long, along with a bright security light shining into bedrooms that comes on each time a passerby comes along (every 5 minutes). Light sleepers need to stay in the Windward cottage as the bedrooms are not on the driveway side with bright light and noise traveling up the alley.
If renting only one of these properties, the Windward is far superior with an open layout for congregating near the kitchen and a cleaned-up back patio. Neither of them are great for very many people gathering for drinks, dinner, or lunch as they do not have a dining room table. Important if you plan to cook and eat with each other. If you are like us and spent most of your time out-and-about then these work great.
Items that may not influence most: Really liked the large mirrors in every room for making it easier for multiple people (girls) to get ready for an evening. We didn't use the hot tubs as it was super hot already in April. I'm not sure if that added expense of cottage with a hot tub fee is worth it unless in the winter. I want to note this is the first rental I've stayed in that didn't have a washer and dryer for us to use throughout the stay. Also, limited hangers and space for clothes and no dresser to put away clothes. For longer stays I felt these things are handy for not "living out of a suitcase."
5.0
Perfect Rental for 8 Adults
Had an incredible experience at this rental property and would definitely visit again. Came down for a bachelor party (8 total guys) and had an absolute blast. Property team was incredibly helpful and easy to work with. GREAT location to everything.
FAQs
How much does this cabin cost compared to others in Key West?
The average price for a rental in Key West is $502 per night. This rental is $879 above the average.
Is parking included with this cabin?
Parking is not specified as an available amenity at Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cabin?
We didn’t find pool listed as an amenity for this cabin. It may be worth double checking if a pool is important for your stay.
Is Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK pet friendly?
Yes! This cabin is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK?
We found 5 amenities for this rental. This includes air conditioner, pets allowed, kitchen / kitchenette, internet / wifi, and hot tub / spa.
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Looking to create some memories in Key West? Look no further than our Bed and Breakfast, Fantastic Land and Sea Vacation! 3 Convenient Units, Onsite Pool. Enjoy top-rated amenities including Air conditioner, Laundry and Kitchen / Kitchenette, and more.
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Hotel
in Key West3x Deluxe Pool View Two Queen Beds at 24 North Hotel Key West
12 guests · 3 bedrooms · 3 baths
Pool · Kitchen / Kitchenette · Air conditioner
Hotel in Key West, for $1,154 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
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Bed and Breakfast
in Key WestFantastic Land and Sea Vacation! 3 Relaxing Spaces, Outdoor Pool
12 guests · 3 bedrooms · 3 baths
Pool · Kitchen / Kitchenette · Air conditioner
Looking to create some memories in Key West? Look no further than our Bed and Breakfast, Fantastic Land and Sea Vacation! 3 Relaxing Spaces, Outdoor Pool. Enjoy top-rated amenities including Air conditioner, Laundry and Kitchen / Kitchenette, and more.
$$$$
Hotel
in Key West3 Standard 2 Queens Rooms at The Gates Hotel Key West
12 guests · 3 bedrooms · 3 baths
Pool · Kitchen / Kitchenette · Air conditioner
Business stays, family stays, couples stay, getaway vacation, and rental in Key West at 3 Standard 2 Queens Rooms at The Gates Hotel Key West for $1,299 for your next trip.
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